Certain-3-amino-2-pyridine-sulfonamide intermediates

ABSTRACT

N-Pyridinesulfonyl-N&#39;-pyrimidinyl- and -triazinylureas of the formula I ##STR1## in which R 1  and R 2  independently of one another are hydrogen, C 1  -C 8  alkyl or C 3  -C 8  cycloalkyl; C 2  -C 8  alkyl or C 3  -C 8  cycloalkyl, each of which is monosubstituted or polysubstituted by halogen; C 1  -C 8  alkyl or C 3  -C 8  cycloalkyl, each of which is substituted by --NR 5  R 6 , C 1  -C 4  alkoxy or C 1  -C 4  alkyl--S(O) n  --; C 1  -C 4  alkyl or C 3  -C 6  cycloalkyl, each of which is substituted by C 2  -C 4  alkenyl, C 5  -C 6  cycloalkenyl, C 2  -C 6  alkynyl or C 4  -C 8  alkadienyl; it being possible for the C 2  -C 4  alkenyl, C 5  -C 6  cycloalkenyl and C 4  -C 8  alkadienyl radicals to be monosubstituted or polysubstituted by halogen; or R 1  and R 2  together are a 4-5-membered C 4  -C 10  alkylene chain which can be interrupted by oxygen, sulfur or N--R.sub. 7 ; R 3  is hydrogen, halogen, C 1  -C 4  alkyl, C 1  -C 4  alkoxy or C 1  -C 4  alkylthio; C 1  -C 4  alkyl, C 1  -C 4  alkoxy or C 1  -C 4  alkylthio, each of which is monosubstituted or polysubstituted by halogen; R 4 , R 5 , R 6  and R 7  independently of one another are hydrogen or C 1  -C 4  alkyl; n is 0, 1 or 2; X is C 1  -C 3  alkyl, or C 1  -C 3  alkyl which is monosubstituted to trisubstituted by halogen; C 1  -C 3  alkoxy, or C 1  -C 3  alkoxy which is monosubstituted to trisubstituted by halogen; Y is halogen, C 1  -C 3  alkyl or C 1  -C 3  alkyl which is monosubstituted to trisubstituted by halogen; C 1  -C 3  alkoxy, or C 1  -C 3  alkoxy which is monosubstituted to trisubstituted by halogen; cyclopropyl, methylamino or dimethylamino; and E is nitrogen or the methine group, and the salts of these compounds with amines, alkali metal bases or alkaline earth metal bases or with quaternary ammonium bases have good selective herbicidal and growth-regulating properties when used pre- and post-emergence.

This is a Divisional of Ser. No. 07/705,459, filed May 24, 1991 U.S.Pat. No. 5,221,315.

The present invention relates to novel, herbicidally active andplant-growth-regulating N-pyridinesulfonyl-N'-pyrimidinyl- and-triazinylureas, processes for their preparation, compositionscontaining them as active substances, and their use for controllingweeds, especially selectively in crops of useful plants or forregulating and inhibiting plant growth.

Urea compounds, triazine compounds and pyrimidine compounds which have aherbicidal action are generally known. For example, European Patent No.103 543 and U.S. Pat. No. 4,544,401 describe herbicidally active andplant-growth-regulating N-pyridinesulfonyl-N'-pyrimidinyl- and-triazinylureas. However, the active substances disclosed therein cannotalways meet the requirements as far as power and selectivity areconcerned. There is hence a demand for active substances which have abetter activity and are more selective.

Novel sulfonylureas which have improved herbicidal andplant-growth-regulating properties have now been found.

The N-pyridinesulfonyl-N'-pyrimidinyl- and triazinylureas according tothe invention are those of the formula I ##STR2## in which R₁ and R₂independently of one another are hydrogen, C₁ -C₈ alkyl or C₃ -C₈cycloalkyl; C₂ -C₈ alkyl or C₃ -C₈ cycloalkyl, each of which ismonosubstituted or polysubstituted by halogen; C₁ -C₈ alkyl or C₃ -C₈cycloalkyl, each of which is substituted by --NR₅ R₆, C₁ -C₄ alkoxy orC₁ -C₄ alkyl--S(O)_(n) --; C₁ -C₄ alkyl or C₃ -C₆ cycloalkyl, each ofwhich is substituted by C₂ -C₄ alkenyl, C₅ -C₆ cycloalkenyl, C₂ -C₆alkynyl or C₄ -C₈ alkadienyl; it being possible for the C₂ -C₄ alkenyl,C₅ -C₆ cycloalkenyl and C₄ -C₈ alkadienyl radicals to be monosubstitutedor polysubstituted by halogen; or R₁ and R₂ together are a 4-5-memberedC₄ -C₁₀ alkylene chain which can be interrupted by oxygen, sulfur orN--R₇ ; R₃ is hydrogen, halogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy or C₁ -C₄alkylthio; C₁ -C₄ alkyl, C₁ -C₄ alkylthio, each of which ismonosubstituted or polysubstituted by halogen; R₄, R₅, R₆ and R₇independently of one another are hydrogen or C₁ -C₄ alkyl; n is 0, 1 or2; X is C₁ -C₃ alkyl, or C₁ -C₃ alkyl which is monosubstituted totrisubstituted by halogen; C₁ -C₃ alkoxy, or C₁ -C₃ alkoxy which ismonosubstituted to trisubstituted by halogen; Y is halogen, C₁ -C₃ alkylor C₁ -C₃ alkyl which is monosubstituted to trisubstituted by halogen;C₁ -C₃ alkoxy, or C₁ -C₃ alkoxy which is monosubstituted totrisubstituted by halogen; cyclopropyl, methylamino or dimethylamino;and E is nitrogen or the methine group, and the salts of thesecompounds.

The alkyl groups which occur as, or in, the substituents R₁ to R₇ can bestraight-chain or branched and are, for example, methyl, ethyl,n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl,n-pentyl or the pentyl isomers, n-hexyl or the hexyl isomers, n-heptylor the heptyl isomers, and also n-octyl or the octyl isomers. The alkylgroups which occur as, or in, the substituents preferably have 1-4carbon atoms.

The alkyl groups which are monosubstituted or polysubstituted by halogenand which occur as, or in, the substituents R₁ -R₃ embracestraight-chain or branched alkyl groups such as methyl, ethyl, n-propyl,iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, n-pentyl, thepentyl isomers, n-hexyl as well as the hexyl isomers, n-heptyl or theheptyl isomers, as well as n-octyl or the octyl isomers, each of thesegroups being monosubstituted or polysubstituted by halogen, halogenspecifically meaning fluorine, chlorine, bromine or iodine.

From amongst these alkyl groups which are monosubstituted orpolysubstituted by halogen, alkyl groups which are monosubstituted totrisubstituted by halogen are preferred. Preferred halogen atoms whichcan occur as substituents of the alkyl groups are fluorine and chlorine.Especially preferred alkyl groups which are monosubstituted orpolysubstituted by halogen are trifluoromethyl, 1-fluoroethyl,1,1-dichloroethyl, 3,3,3-trifluoropropyl, 2-fluoroisopropyl,3-fluoropropyl, 1,1,1-trichloropentyl, 1-fluoro-3-methylpentyl or1-bromohexyl. 3-Fluoropropyl and 2-fluoroisopropyl are very particularlypreferred.

The C₁ -C₃ alkyl radicals which occur as, or in, the substituents X andY specifically embrace methyl, ethyl, n-propyl and iso-propyl, as wellas the haloalkyls which are monosubstituted to trisubstituted by halogenand which are derived from these radicals. The alkyl radicals whichoccur as, or in, the substituents X and Y preferably have one to twocarbon atoms.

Preferred groups amongst the C₁ -C₃ alkyl groups which aremonosubstituted to trisubstituted by halogen and which occur as, or in,the substituents X and Y are C₁ -C₂ alkyl groups which aremonosubstituted to trisubstituted by fluorine or chlorine. Especiallypreferred C₁ -C₃ alkyl radicals which are monosubstituted totrisubstituted by halogen and which occur as, or in, the substituents Xand Y are: trifluoromethyl, difluoromethyl, 2-chloroethyl,chlorodifluoromethyl, dichloromethyl, chlorofluoromethyl,1,1-dichloroethyl, trifluoroethyl, 3,3,3-trifluoropropyl or2,3-dichloropropyl, particularly preferred are fluoromethyl,chloromethyl, difluoromethyl and trifluoromethyl.

The C₂ -C₄ alkenyl radicals which occur in the substituents R₁ and R₂can be in the Z form (cis) or in the E form (trans) and can bestraight-chain or branched. Preferred alkenyl radicals are those havinga chain length of two to three carbon atoms. Examples of C₂ -C₄ alkenylradicals are: vinyl, allyl, methallyl, 1-methylvinyl and but-2-en-1-yl.Vinyl and allyl are preferred. In the case of the C₂ -C₄ alkenylradicals which are monosubstituted or polysubstituted by halogen,halogen is, specifically, fluorine, chlorine, bromine and iodine.Preferred halogen atoms which can occur as substituents of the C₂ -C₄alkenyl radicals are fluorine and chlorine. Preferred radicals amongstthe C₂ -C₄ alkenyl radicals which are monosubstituted to trisubstitutedby halogen are those which have a chain length of two to three carbonatoms. Especially preferred C₂ -C₄ alkenyl radicals which aremonosubstituted to trisubstituted by halogen are 1-chlorovinyl,2-chlorovinyl, 3-fluoroallyl and 4,4,4-trifluoro-but-2-en-1-yl.1-Chlorovinyl and 2-chlorovinyl are very particularly preferred.

The C₄ -C₈ alkadienyl radicals which can be monosubstituted orpolysubstituted by halogen and which occur in the substituents R₁ and R₂are, for example, buta-1,3-dienyl, penta-1,3-dienyl, hexa-3,5-dienyl,hepta-4,6-dienyl, octa-1,7-dienyl, 4-chlorobuta-1,3-dienyl, or5,5,5-trifluoropenta-1,3-dienyl.

The C₂ -C₆ alkynyl radicals which occur in the definitions of thesubstitutents R₁ and R₂ can be straight-chain or branched. Preferredalkynyl radicals are those which have a chain length of two to threecarbon atoms. C₂ -C₄ Alkynyl radicals are, for example, ethynyl,propargyl, 1-propynyl, 3-butynyl, 1-methylpropargyl, 3-pentynyl or3-hexynyl, ethynyl and propargyl being particularly preferred.

The cycloalkyl groups which are unsubstituted or monosubstituted orpolysubstituted by halogen and which occur in the substituents R₁ and R₂embrace, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cycloheptyl, cyclooctyl, 2-fluorocyclopropyl, 2,3-diflurocyclopropyl,2,2-dichlorocyclopropyl, 3-bromocyclopropyl, 2,3,4-trifluorocyclopentylor 2,3-dichlorocyclohexyl. Preferred amongst these cycloalkyl groups arethe cyclopropyl, cyclopentyl and cyclohexyl groups which aremonosubstituted to disubstituted by halogen, halogen being fluorine,chlorine, bromine and iodine, but in particular fluorine and chlorine.

Examples of other substituted cycloalkyl groups are2-methoxycyclopropyl, 3-ethylthiocyclobutyl,2-methylsulfonylcyclopentyl, 3-ethylsulfinylcyclohexyl,4-(2,4-pentadienyl)-cyclohexane, 3-aminocyclohexyl, 4-allylcyclohexyl or3-propargylcyclohexyl.

The C₅ -C₆ cycloalkenyl radicals can be monosubstituted totrisubstituted by halogen. Preferred halogen atoms here are fluorine andchlorine. Examples of C₅ -C₆ cycloalkenyl radicals are 3-cyclopentene,2-cyclopentene, 4-chlorocyclopent-3-ene, 3,4-difluorocyclopent-3-ene,2-cyclohexene, 3-cyclohexene, 4,5-dibromocyclohex-2-ene or4,4,5-trifluorocyclohex-2-ene.

Examples of heterocycles which can, together with the nitrogen atom towhich they are bonded, form the substituents R₁ and R₂ are: pyrrolidine,3-methylpyrrolidine, imidazolidine, piperidine, 3-isopropylpiperidine,piperazine, 4-methylpiperazine, 4-ethylpiperazine,4-isopropylpiperazine, morpholine, oxazolidine, and thiazolidine. It ispreferred for the substituents R₁ and R₂ to form 4-5 -membered C₄ -C₅alkylene chains. Preferred heterocycles which can, together with thenitrogen atom to which they are bonded, form the substituents R₁ and R₂are: 4-methylpiperazine, morpholine and piperidine.

Alkylthio is, for example, methylthio, ethylthio, propylthio,isopropylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio or thepentylthio isomers, preferably methylthio and ethylthio.

Alkoxy is, for example, methoxy, ethoxy, propyloxy, i-propyloxy,n-butyloxy, i-butyloxy, s-butyloxy and t-butyloxy; preferably methoxyand ethoxy.

The invention also embraces the salts which the compounds of the formulaI can form together with amines, alkali metal bases and alkaline earthmetal bases or quaternary ammonium bases.

Salt formers which must be emphasised amongst alkali metal hydroxidesand alkaline earth metal hydroxides are the hydroxides of lithium,sodium, potassium, magnesium or calcium, but in particular those ofsodium or potassium.

Examples of amines which are suitable for salt formation are primary,secondary and tertiary aliphatic and aromatic amines such asmethylamine, ethylamine, propylamine, isopropylamine, the fourbutylamine isomers, dimethylamine, diethylamine, diethanolamine,dipropylamine, diisopropylamine, di-n-butylamine, pyrrolidine,piperidine, morpholine, trimethylamine, triethylamine, tripropylamine,quinuclidine, pyridine, quinoline and isoquinoline, but in particularethyl-, propyl-, diethyl- or triethylamine, but above all isopropylamineand diethanolamine.

Examples of quaternary ammonium bases are, generally, the cations ofammonium halide salts, for example the tetramethylammonium cation, thetrimethylbenzylammonium cation, the triethylbenzylammonium cation, thetetraethylammonium cation, the trimethylethylammonium cation, but alsothe ammonium cation.

Compounds from within the scope of the formula I which must beemphasised are those in which R₁ and R₂ independently of one another arehydrogen, C₁ -C₈ alkyl or C₃ -C₈ cycloalkyl; C₂ -C₈ alkyl or C₃ -C₈cycloalkyl which are monosubstituted or polysubstituted by halogen; C₁-C₈ alkyl or C₃ -C₈ cycloalkyl which are substituted by --NR₅ R₆, C₁ -C₄alkoxy or C₁ -C₄ alkyl--S(O)_(n) --; C₁ -C₄ alkyl or C₃ -C₆ cycloalkylwhich are substituted by C₂ -C₄ alkenyl, C₅ -C₆ cycloalkenyl, C₂ -C₆alkynyl or C₄ -C₈ alkadienyl; it being possible for the C₂ -C₄ alkenyl,C₅ -C₆ cycloalkenyl and C₄ -C₈ alkadienyl radicals to be monosubstitutedor polysubstituted by halogen.

Other preferred compounds from amongst those of the formula I are thosein which R₁ and R₂ independently of one another are hydrogen, C₁ -C₆alkyl or C₃ -C₆ cycloalkyl; C₂ -C₆ alkyl or C₃ -C₆ cycloalkyl which aremonosubstituted to trisubstituted by halogen; C₁ -C₆ alkyl or C₃ -C₆cycloalkyl which are substituted by --NR₅ R₆, C₁ -C₄ alkoxy or C₁ -C₄alkyl--S(O)_(n) --; C₁ -C₄ alkyl or C₃ -C₆ cycloalkyl which aresubstituted by C₂ -C₄ alkenyl, C₅ -C₆ cycloalkenyl, C₂ -C₄ alkynyl or C₄-C₈ alkadienyl; it being possible for the C₂ -C₄ alkenyl, C₅ -C₆cycloalkenyl and C₄ -C₈ alkadienyl radicals to be monosubstituted totrisubstituted by halogen; and R₃ is hydrogen, halogen, C₁ -C₄ alkyl, C₁-C₄ alkoxy or C₁ -C.sub. 4 alkylthio; or C₁ -C₄ alkyl, C₁ -C₄ alkoxy orC₁ -C₄ alkylthio which are monosubstituted to trisubstituted by halogen.

Furthermore, compounds amongst those of the formula I which are ofparticular interest are those in which at least one of the substitutentsR₁ R₂ and R₃ is other than hydrogen.

Very particularly preferred groups of compounds of the formula I arethose in which

a) X is C₁ -C₃ alkyl, C₁ -C₃ alkoxy or C₁ -C₃ alkoxy which ismonosubstituted to trisubstituted by halogen; and Y is chlorine, C₁ -C₃alkyl, C₁ -C₃ alkoxy or C₁ -C₃ alkoxy which is monosubstituted totrisubstituted by halogen; or

b) X is methyl, methoxy, ethoxy or difluoromethoxy; and Y is methyl,methoxy, ethoxy, difluoromethoxy or chlorine; or

c) X is methoxy or ethoxy; and Y is methyl or methoxy;

d) E is the methine bridge; or

e) R₃ is in the 6-position of the pyridine ring; or

f) R₃ is hydrogen.

From amongst these compounds, compounds in which

a) R₂ and R₃ are hydrogen and R₁ is C₁ -C₆ alkyl or C₃ -C₆ cycloalkyl;C₂ -C₆ alkyl or C₃ -C₆ cycloalkyl which are monosubstituted totrisubstituted by halogen; C₁ -C₆ alkyl or C₃ -C₆ cycloalkyl which aresubstituted by --NR₅ R₆, C₁ -C₄ alkoxy or C₁ -C₄ alkyl--S(O)_(n) --; C₁-C₄ alkyl or C₃ -C₆ cycloalkyl which are substituted by C₂ -C₄ alkenyl,C₅ -C₆ cycloalkenyl, C₂ -C₄ alkynyl or C₄ -C₈ alkadienyl; it beingpossible for the C₂ -C₄ alkenyl, C₅ -C₆ cycloalkenyl and C₄ -C₈alkadienyl radicals to be monosubstituted to trisubstituted by halogen;or

b) R₁ is C₁ -C₆ alkyl, allyl or propargyl, and R₂ is hydrogen, methyl orallyl, must be particularly emphasised.

From within the scope of the formula I, mention must be made ofN-(3-n-butylaminopyridin-2-ylsulfonyl)-N'-(4,6-dimethoxypyrimidin-2-yl)ureaas a particularly preferred single compound.

The compounds of the formula I can be prepared by reacting

a) a pyridylsulfonamide of the formula II ##STR3## in which R₁, R₂ andR₃ are as defined under formula I in claim 1, with an N-pyrimidinyl orN-triazinylcarbamate of the formula III ##STR4## in which X, Y, R₄ and Eare as defined under formula I in claim 1 and R₈ is C₁ -C₄ alkyl, orphenyl which can be substituted by C₁ -C₄ alkyl or halogen, in thepresence of a base, or

b) a pyridylsulfonamide of the formula XII ##STR5## in which R₁ ', R₂ 'are as defined under R₁ and R₂ in formula I in claim 1, with theexception of hydrogen, R₃ is as defined under formula I in claim 1, andA is ##STR6## R₈ being as defined above, with a 2-aminopyrimidine or-triazine of the formula XI ##STR7## in which E, X and Y are as definedunder formula I, in the presence of a base.

Compounds of the formula Ia ##STR8## in which R₁, R₂, R₃, R₄ and E areas defined under formula I and X₁ and Y₁ independently of one anotherare chlorine or difluoromethoxy, can be prepared by reacting apyridylsulfonamide of the formula II ##STR9## in which R₁, R₂ and R₃ areas defined under formula I in claim 1, with a pyrimidinyl or triazinylisocyanate of the formula IV ##STR10## in which X₁ and Y₁ are as definedunder formula Ia and E is as defined under formula I, in the presence ofa base.

The reactions to give compounds of the formula I are advantageouslycarried out in aprotic, inert organic solvents. Such solvents arehydrocarbons such as benzene, toluene, xylene or cyclohexane,chlorinated hydrocarbons such as dichloromethane, trichloromethane,tetrachloromethane or chlorobenzene, ethers such as diethyl ether,ethylene glycol dimethyl ether, diethylene glycol dimethyl ether,tetrahydrofuran or dioxane, nitriles such as acetonitrile orpropionitrile and amides such as dimethylformamide, diethylformamide orN-methylpyrrolidinone. The reaction temperatures are preferably between-20° and +120° C.

In general, the reactions proceed slightly exothermcally and can becarried out at room temperature. To shorten the reaction time, or,alternatively, to initiate the reaction, it is expedient to heat thereaction mixture briefly to boiling point. It is equally possible toshorten the reaction times by adding a few drops of base as a reactioncatalyst. Suitable bases are, in particular, tertiary amines such astrimethylamine, triethylamine, quinuclidine,1,4-diazabicyclo[2.2.2]-octane, 1,5-diazabicyclo[4.3.0]non-5-ene or1,5-diazabicyclo[5.4.0]undec-7-ene. Alternatively, inorganic bases, suchas hydrides, such as sodium hydride or calcium hydride, hydroxides suchas sodium hydroxide and potassium hydroxide, carbonates such as sodiumcarbonate and potassium carbonate, or hydrogen carbonates such aspotassium hydrogen carbonate and sodium hydrogen carbonate, can also beused as bases.

The end products of the formula I can be isolated by concentrationand/or by evaporation of the solvent and purified by recrystallisationor trituration of the solid residue in solvents in which they are notreadily soluble, such as ethers, aromatic hydrocarbons or chlorinatedhydrocarbons.

The intermediates of the formulae XII, III and IV are known or can beprepared analogously to known processes. Processes for the preparationof N-pyrimidinyl-and N-triazinylcarbamates are described, for example,in EP-A 0 101 670. N-Pyrimidinyl and N-triazinyl isocyanates can beprepared from the corresponding 2-aminopyrimidines or -triazines of theformula XI. Reactions of this type as well as the preparation of thecompounds of the formula XII are described in EP-A 0 044 808. Compoundsof the formula XI are disclosed in EP-A 0 070 804. With the exception ofthe compound in which R₁, R₂ and R₃ are hydrogen, the intermediates ofthe formula II are novel and were developed specifically forsynthesising the compounds of the formula I. They form therefore a partof the present invention.

The novel intermediates of the formula II can be prepared by variousmethods which are known per se. For example, the compounds of theformula II are obtained by reacting a 3-halopyridin-2-ylsulfonamide ofthe formula V ##STR11## in which R₃ is as defined under formula I andHal is fluorine or chlorine, with an amine of the formula VI ##STR12##in which R₁ and R₂ are as defined under formula I, in the presence of abase. Preferred compounds for these reactions are those compounds of theformula V in which Hal is fluorine. Syntheses of this type aredescribed, for example, in EP-A 103 543.

Alternatively, the compounds of the formula II can be prepared byreacting a 3-aminopyridin-2-ylsulfonamide of the formula VII ##STR13##in which R₃ is as defined under formula I, with a compound of theformula VIII

    Z--R.sub.1                                                 (VIII)

in which R₁ is as defined under formula I and Z is bromine, iodine,##STR14## in the presence of a base, to give the compound of the formulaIX ##STR15## in which R₃ is as defined under formula I, and subsequentlyreacting this compound with a compound of the formula X

    Z--R.sub.2                                                 (X)

in which R₂ is as defined under formula I and Z is as defined underformula VIII, in the presence of a base, to give the compound of theformula II. Reactions of this type are described, for example in FarmacoEd. scient. 12, 392 (1957). The sulfonamide intermediates of theformulae V and VII are known. They can be prepared, for example,analogously to J. Pharm. Belg. 39, 217-224 (1984).

As a rule, the active substances of the formula I are sucessfullyemployed at application rates from 0.001 to 2 kg/ha, in particular 0.005to 1 kg/ha. The dosage rate which is required for the desired action canbe determined by tests. It depends on the nature of the action, thedevelopment stage of the crop plant and the weed, as well as on theapplication (location, time, method) and, due to these parameters, canvary within wide limits.

Used at low application rates, the compounds of the formula I aredistinguished by growth-inhibiting and herbicidal properties, which makethem outstandingly suitable for use in crops of useful plants, inparticular in cereals, cotton, soybeans, oilseed rape, corn and rice,the use in corn crops being very particularly preferred.

The invention also relates to herbicidal and plant-growth-regulatingcompositions which comprise a novel active substance of the formula I,as well as methods for inhibiting plant growth.

Plant growth regulators are substances which cause agronomicallydesirable biochemical and/or physiological and/or morphologicalmodifications in/on the plant.

The active substances contained in the compositions according to theinvention affect plant growth in many ways, depending on the point intime of application, the dosage rate, the type of application and theprevailing environment. For example, plant growth regulators of theformula I can inhibit the vegetative growth of plants. This type ofaction is of interest on lawns, in the production of ornamental, inorchards, on verges, on sports grounds and industrial terrain, but alsoin the targeted inhibition of secondary shoots, such as in tobacco. Inarable farming, inhibition of the vegetative growth in cereals bystrengthening the stem results in reduced lodging, and similaragronomical effects are achieved in oilseed rape, sunflowers, maize andother crop plants. Furthermore, inhibition of the vegetative growthmeans that the number of plants per unit area can be increased. Anotherfield in which growth inhibitors can be applied is the selective controlof ground-cover plants, in plantations or crops with plenty of spacebetween the rows, by powerful growth inhibition without destroying thesecover crops, so that competition with the main crop is eliminated, butthe agronomically positive effects, such as reduction of erosion,nitrogen fixation and loosening of the soil, are retained.

A method for inhibiting plant growth is understood as meaningcontrolling the natural development of the plant without altering thelife cycle of the plant, which is determined by its genetic make-up, inthe sense of a mutation. The method of growth regulation is applied at aparticular point in time of the development of the plant, which is to bedetermined in the particular case. The active substances of the formulaI can be applied before or after emergence of the plants, for examplealready to the seeds or seedlings, to roots, tubers, stalks, leaves,flowers or other parts of the plants. This can be effected, for example,by applying the active substance, as such or in the form of acomposition, to the plants and/or by treating the nutrient substrate ofthe plant (soil).

Various methods and techniques are suitable for using the compound ofthe formula I or compositions containing it for regulating plant growth,for example the following:

i) Seed treatment

a) The seeds are treated with an active substance formulated as awettable powder by shaking in a container until the seed surface isuniformly covered (dry seed treatment). Up to 4 g of active substance ofthe formula I are used per kg of seed in this method (up to 8.0 g ofwettable powder in the case of a 50% formulation).

b) Treating the seeds with an emulsion concentrate of the activesubstance or with an aqueous solution of the active substance of theformula I formulated as a wettable powder, using method a) (wet seedtreatment).

c) Seed treatment by immersing the seeds in a liquor containing up to1000 ppm of active substance of the formula I for 1 to 72 hours, which,if desired, is followed by drying the seeds (seed soaking).

Naturally, seed treatment or treatment of the germinated seedling arethe preferred application methods since the treatment with activesubstance is directed entirely at the target crop. 0.001 g to 4.0 g ofactive compound are generally used per kg of seed, but it is possible todeviate from the limit concentrations given in both directions,depending on the method chosen which also makes possible the addition ofother active substances or micronutrients (repeated seed treatment).

ii) Controlled release of active substance

The dissolved active substance is applied to mineral granule carriers orpolymerised granules (urea/formaldehyde) and allowed to dry. If desired,a coating can be applied (coated granules), which permits slow releaseof the active substance over a certain period.

The compounds of the formula I are employed in unaltered form, asobtainable by the synthesis, or preferably together with the auxiliariesconventionally used in formulation technology, and they are thereforeprocessed in a known manner to give, for example, emulsifiableconcentrates, directly sprayable or dilutable solutions, diluteemulsions, wettable powders, soluble powders, dusts, granules, and alsoencapsulations, for example in polymeric substances. The applicationmethods, such as spraying, atomising, dusting, scattering or pouring, aswell as the type of compositions are selected to suit the intended aimsand the prevailing circumstances.

The formulations, i.e. the compositions, preparations or combinationscomprising the active substance of the formula I and, if desired, one ormore solid or liquid additives, are prepared in a known manner, forexample by intimately mixing and/or grinding the active substances withextenders, for example with solvents, solid carriers and, if desired,surface-active compounds (surfactants).

The following are possible as solvents: aromatic hydrocarbons, inparticular the fractions C₈ to C₁₂, such as mixtures of alkylbenzenes,for example xylene mixtures or alkylated naphthalenes; aliphatic andcycloaliphatic hydrocarbons such as paraffins, cyclohexane ortetrahydronaphthalene; alcohols, such as ethanol, propanol or butanol;glycols as well as their ethers and esters, such as propylene glycol ordipropylene glycol ether, ketones such as cyclohexanone, isophorone ordiacetone alcohol, strongly polar solvents such asN-methyl-2-pyrrolidone, dimethyl sulfoxide or water; vegetable oils aswell as their esters, such as rapeseed oil, castor oil or soybean oil;and if appropriate also silicone oils.

Solid carriers which are generally used, for example for dusts anddispersible powders, are ground natural minerals, such as calcite, talc,kaolin, montmorillonite or attapulgite. To improve the physicalproperties, it is also possible to add highly-disperse silica orhighly-disperse absorptive polymers. Possible particulate, adsorptivecarriers for granules are either porous types, for example pumice, brickgrit, sepiolite or bentonite, or non-sorptive carrier materials, such ascalcite or sand. Moreover, a large number of pregranulated materials ofinorganic or organic nature can be used, such as, in particular,dolomite or comminuted plant residues.

Suitable surface-active compounds are non-ionic, cationic and/or anionicsurfactants having good emulsifying, dispersing and wetting properties,depending on the nature of the active substance of the formula I to beformulated. Surfactants are also to be understood as meaning mixtures ofsurfactants.

Anionic surfactants which are suitable can be either so-calledwater-soluble soaps or water-soluble synthetic surface-active compounds.Suitable soaps which may be mentioned are the alkali metal salts,alkaline earth metal salts or substituted or unsubstituted ammoniumsalts of higher fatty acids (C₁₀ -C₂₂), such as the Na salts or K saltsof oleic or stearic acid, or of natural mixtures of fatty acids whichcan be obtained, for example, from coconut oil or tallow oil. Mentionmust also be made of the fatty acid methyltaurinates.

However, so-called synthetic surfactants are used more frequently, inparticular fatty alcohol sulfonates, fatty alcohol sulfates, sulfonatedbenzimidazole derivatives or alkylarylsulfonates.

The fatty alcohol sulfonates or fatty alcohol sulfates are generally inthe form of alkali metal salts, alkaline earth metal salts orsubstituted or unsubstituted ammonium salts, and have an alkyl radicalhaving 8 to 22 C atoms, alkyl also including the alkyl moiety of acylradicals, for example the Na or Ca salt of ligninsulfonic acid, of thedodecylsulfuric ester or of a fatty alcohol sulfate mixture preparedfrom natural fatty acids. This group also includes the salts of thesulfuric esters and sulfonic acids of fatty alcohol/ethylene oxideadducts. The sulfonated benzimidazole derivatives preferably contain 2sulfonyl groups and one fatty acid radical having 8 to 22 C atoms.Examples of alkylarylsulfonates are the Na, Ca or triethanolamine saltsof dodecylbenzenesulfonic acid, of dibutylnaphthalenesulfonic acid or ofa naphthalenesulfonic acid/formaldehyde condensation product.

Other suitable compounds are the corresponding phosphates, such as thesalts of the phosphoric ester of a p-nonylphenol/(4-14)-ethylene oxideadduct, or phospholipids.

Suitable non-ionic surfactants are mainly polyglycol ether derivativesof aliphatic or cycloaliphatic alcohols, of saturated or unsaturatedfatty acids and of alkylphenols, which can contain 3 to 30 glycol ethergroups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radicaland 6 to 18 carbon atoms in the alkyl radical of the alkylphenols.

Other non-ionic surfactants which are suitable are the water-solublepolyethylene oxide adducts with polypropylene glycol,ethylenediaminopolypropylene glycol and alkylpolypropylene glycol whichhave 1 to 10 carbon atoms in the alkyl chain and which contain 20 to 250ethylene glycol ether groups and 10 to 100 propylene glycol ethergroups. The abovementioned compounds customarily contain 1 to 5 ethyleneglycol units per propylene glycol unit. Examples of non-ionicsurfactants which may be mentioned are nonylphenolpolyethoxyethanols,castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts,tributylphenoxypolyethoxyethanol, polyethylene glycol andoctylphenoxypolyethoxyethanol.

Other suitable substances are fatty acid esters ofpolyoxyethylenesorbitan, such as polyoxyethylenesorbitan trioleate.

The cationic surfactants are mainly quaternary ammonium salts, whichcontain at least one alkyl radical having 8 to 22 C atoms asN-substituents and which have lower halogenated or free alkyl, benzyl orlower hydroxyalkyl radicals as further substituents. The salts arepreferably in the form of halides, methylsulfates or ethylsulfates, forexample stearyltrimethylammonium chloride orbenzyldi(2-chloroethyl)ethylammonium bromide.

The surfactants customary in formulation technology are described, interalia, in the following publications:

"McCutcheon's Detergents and Emulsifiers Annual", Mc Publishing Corp.,Glen Rock, N.J., 1988;

M. and J. Ash. "Encyclopedia of Surfactants", Vol. I-III, ChemicalPublishing Co., New York, 1980-1981.

Dr. Helmut Stache, "Tensid-Taschenbuch [Surfactant Guide]", Carl HanserVerlag, Munich, Vienna, 1981;

As a rule, the pesticidal preparations contain 0.1 to 99%, in particular0.1 to 95%, of the active substance of the formula I, 1 to 99% of asolid or liquid additive and 0 to 25%, in particular 0.1 to 25%, of asurfactant.

While concentrated compositions are more preferred as commercial goods,the user generally uses dilute compositions.

The compositions can also comprise further additives such asstabilisers, for example epoxidised or unepoxidised vegetable oils(epoxidised coconut oil, repeseed oil or soybean oil), defoamers, forexample silicone oil, preservatives, viscosity regulators, binders,tackifiers, as well as fertilisers or other active substances forachieving specific effects.

In particular, preferred formulations have the following composition:(%=percent by weight)

    ______________________________________                                        Emulsifiable concentrates:                                                    Active ingredient:                                                                           1 to 90%, preferably 5 to 20%                                  Surface-active 1 to 30%, preferably 10 to 20%                                 agent:                                                                        Liquid carrier:                                                                              50 to 94%, preferably 70 to 85%                                Dusts:                                                                        Active ingredient:                                                                           0.1 to 10%, preferably 0.1 to 1%                               Solid carrier: 99.9 to 90%, preferably 99.9 to 99%                            Suspension concentrates:                                                      Active ingredient:                                                                           5 to 75%, preferably 10 to 50%                                 Water:         94 to 24%, preferably 88 to 30%                                Surface-active 1 to 40%, preferably 2 to 30%                                  agent:                                                                        Wettable powders:                                                             Active ingredient:                                                                           0.5 to 90%, preferably 1 to 80%                                Surface-active 0.5 to 20%, preferably 1 to 15%                                agent:                                                                        Solid carrier material:                                                                      5 to 95%, preferably 15 to 90%.                                Granules:                                                                     Active ingredient:                                                                           0.5 to 30%, preferably 3 to 15%                                Solid carrier material:                                                                      99.5 to 70%, preferably 97 to 85%.                             ______________________________________                                    

PREPARATION EXAMPLES EXAMPLE H1 Preparation ofN-(3-n-butylaminopyridin-2-ylsulfonyl)-N'-(4,6-dimethoxypyrimidin-2-yl)urea(compound No. 1.001) ##STR16##

The following are added in succession to a mixture of 2.75 g of3-n-butylaminopyridin-2-ysulfonamide in 40 ml of acetonitrile: 3.5 g ofphenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate and 1.97 ml of1,5-diazabicyclo[5.4.0]undec-5-ene. The reaction mixture is stirred for30 minutes and evaporated, the oily residue is triturated with 10 ml of2N hydrochloric acid and subsequently with 10 ml of ice/water and alittle diethyl ether, and the mixture is filtered. The filter residue issubsequently washed with a little water and diethyl ether and dried.4.39 g ofN-(3-n-butylaminopyridin-2-ylsulfonyl)-N'-(4,6-dimethoxypyrimidin-2-yl)urea(compound No. 1.001) of a melting point of 118°-119° C. are obtained.

EXAMPLE H2 Preparation of 3-n-butylaminopyridin-2-ylsulfonamide(intermediate No. 2.001) ##STR17##

49.6 ml of n-butylamine are added to a mixture of 8.81 g of3-fluoropyridin-2-ylsulfonamide in 10 ml of tetrahydrofuran (THF). Afterthe reaction mixture has been stirred for 18 hours at a temperature of60° C., the reaction mixture is evaporated, the oily residue istriturated with 100 ml of ice/water, the mixture is filtered, and thefiltrate is washed first with a little cold water and subsequently withn-hexane. After drying at a temperature of 45° C. in vacuo, 8.8 g of3-n-butylaminopyridin-2-ylsulfonamide (intermediate No. 2.001) of amelting point of 100°-101° C. are obtained.

EXAMPLE H3 Allylaminopyridin-2-ylsulfonamide (intermediate No. 2.002)##STR18##

5.28 g of 3-fluoropyridin-2-ylsulfonamide and 18.03 ml of allylamine arestirred for 6 hours in a pressurised vessel at a temperature of 125° C.The reaction solution is subsequently concentrated, the crystallisateobtained is dissolved in methylene chloride and a little acetonitrile,the mixture is purified by chromatography using methylene chloride/ethylacetate (4:1) as the eluent mixture and silica gel as the carriermaterial. 5.1 g of 3-allylaminopyridin-2-ylsulfonamide (intermediate No.2.002) of a melting point of 134°-135° C. are obtained.

The compounds of the formula I as well as the intermediates of theformula II which are listed in the appended tables are preparedanalogously.

                                      TABLE 1                                     __________________________________________________________________________     ##STR19##                                   (I)                              No.                                                                              R.sub.1  R.sub.2 R.sub.3                                                                            R.sub.4                                                                          X    Y    E  M.p. [°C.]                    __________________________________________________________________________    1.001                                                                            n-C.sub.4 H.sub.9                                                                      H       H    H  CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH 118-119                              1.002                                                                            n-C.sub.4 H.sub.9                                                                      H       H    H  CH.sub.3 O                                                                         Cl   CH                                      1.003                                                                            n-C.sub.4 H.sub.9                                                                      H       H    H  CH.sub.3 O                                                                         CH.sub.3                                                                           CH                                      1.004                                                                            n-C.sub.4 H.sub.9                                                                      H       H    H  CH.sub.3 O                                                                         CH.sub.3                                                                           N                                       1.005                                                                            n-C.sub.4 H.sub.9                                                                      H       H    H  CH.sub.3 O                                                                         OCHF.sub.2                                                                         CH                                      1.006                                                                            n-C.sub.4 H.sub.9                                                                      H       H    H  CH.sub.3                                                                           OCHF.sub.2                                                                         CH                                      1.007                                                                            n-C.sub.4 H.sub.9                                                                      H       H    H  CH.sub.3 O                                                                         OC.sub.2 H.sub.5                                                                   N                                       1.008                                                                            H        H       H    H  CH.sub.3 O                                                                         CH.sub.3 O                                                                         CH 132-134                              1.009                                                                            H        H       H    H  CH.sub.3 O                                                                         Cl   CH                                      1.010                                                                            H        H       H    H  CH.sub.3 O                                                                         CH.sub.3                                                                           N                                       1.011                                                                            H        H       H    H  CH.sub.3                                                                           OCHF.sub.2                                                                         CH                                      1.012                                                                            CH.sub.3 H       H    H  OCH.sub.3                                                                          Cl   CH 167-169                              1.013                                                                            CH.sub.3 H       H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH 147-148                              1.014                                                                            CH.sub.3 H       H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N  141-143                              1.015                                                                            CH.sub.3 H       H    H  OCH.sub.3                                                                          OCHF.sub.2                                                                         CH                                      1.016                                                                            CH.sub.3 H       H    H  OCHF.sub.2                                                                         OCHF.sub.2                                                                         CH                                      1.017                                                                            CH.sub.3 CH.sub.3                                                                              H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH 134-135                              1.018                                                                            CH.sub.3 H       H    H  OCH.sub.3                                                                          Cl   CH 128-130                              1.019                                                                            CH.sub.3 H       H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N  178-181                              1.020                                                                            CH.sub.3 H       H    H  OCH.sub.3                                                                          OCHF.sub.2                                                                         CH                                      1.021                                                                            CH.sub.3 H       H    H  CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                   N                                       1.022                                                                            CH.sub.3 H       H    H  OCHF.sub.2                                                                         OCHF.sub.2                                                                         CH                                      1.023                                                                            C.sub.2 H.sub.5                                                                        H       H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH 140-141                              1.024                                                                            C.sub.2 H.sub.5                                                                        H       H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N                                       1.025                                                                            C.sub.2 H.sub.5                                                                        H       H    H  OCHF.sub.2                                                                         OCHF.sub.2                                                                         CH                                      1.026                                                                            C.sub.2 H.sub.5                                                                        H       H    H  OCH.sub.3                                                                          Cl   CH                                      1.027                                                                            CH(CH.sub.3).sub.2                                                                     H       H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH 134-135                              1.028                                                                            CH(CH.sub.3).sub.2                                                                     H       H    H  OCH.sub.3                                                                          Cl   CH 118-121                              1.029                                                                            CH(CH.sub.3).sub.2                                                                     H       H    H  OCHF.sub.2                                                                         OCHF.sub.2                                                                         CH                                      1.030                                                                            CH(CH.sub.3).sub.2                                                                     H       H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N  131-133                              1.031                                                                            CH(CH.sub.3).sub.2                                                                     H       H    H  OC.sub.2 H.sub.5                                                                   CH.sub.3                                                                           N                                       1.032                                                                            C.sub.2 H.sub.5                                                                        CH.sub.3                                                                              H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH 124-126                              1.033                                                                            C.sub.2 H.sub.5                                                                        CH.sub.3                                                                              H    H  OCH.sub.3                                                                          Cl   CH                                      1.034                                                                            C.sub.2 H.sub.5                                                                        CH.sub.3                                                                              H    H  OCHF.sub.2                                                                         OCHF.sub.2                                                                         CH                                      1.035                                                                            C.sub.2 H.sub.5                                                                        CH.sub.3                                                                              H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N                                       1.036                                                                            C.sub.2 H.sub.5                                                                        CH.sub.3                                                                              H    H  OC.sub.2 H.sub.5                                                                   CH.sub.3                                                                           N                                       1.037                                                                             CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                              H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH 135-136                              1.038                                                                            CH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                              H    H  OCH.sub.3                                                                          Cl   CH                                      1.039                                                                            CH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                              H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N                                       1.040                                                                            CH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                              H    H  OC.sub.2 H.sub.5                                                                   CH.sub.3                                                                           N                                       1.041                                                                            CH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                              H    H  OCHF.sub.2                                                                         OCHF.sub.2                                                                         CH                                      1.042                                                                            C.sub.4 H.sub.9 -(n)                                                                   CH.sub.3                                                                              H    H  OCHF.sub.2                                                                         OCHF.sub.2                                                                         CH                                      1.043                                                                            C.sub.4 H.sub.9 -(n)                                                                   CH.sub.3                                                                              H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH 126-127                              1.044                                                                            C.sub.4 H.sub.9 -(n)                                                                   CH.sub.3                                                                              H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.045                                                                            C.sub.4 H.sub.9 -(n)                                                                   CH.sub.3                                                                              H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N                                       1.046                                                                            C.sub.4 H.sub.9 -(n)                                                                   CH.sub.3                                                                              H    H  OC.sub.2 H.sub.5                                                                   CH.sub.3                                                                           N                                       1.047                                                                            C.sub.4 H.sub.9 -(n)                                                                   CH.sub.3                                                                              H    H  OCH.sub.3                                                                          Cl   CH                                      1.048                                                                            CH.sub.2 CHCH.sub.2                                                                    H       H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH 130-133                              1.049                                                                            CH.sub.2 CHCH.sub.2                                                                    H       H    H  OCH.sub.3                                                                          Cl   CH                                      1.050                                                                            CH.sub. 2 CHCH.sub.2                                                                   H       H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.051                                                                            CH.sub.2 CHCH.sub.2                                                                    H       H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N  110-113                              1.052                                                                            CH.sub.2 CHCH.sub.2                                                                    H       H    H  OC.sub.2 H.sub.5                                                                   CH.sub.3                                                                           N                                       1.053                                                                            CH.sub.2 CHCH.sub.2                                                                    H       H    H  OCHF.sub.2                                                                         OCHF.sub.2                                                                         CH                                      1.054                                                                            CH.sub.2 CHCH.sub.2                                                                    CH.sub.2 CHCH.sub.2                                                                   H    H  OCHF.sub.2                                                                         OCHF.sub.2                                                                         CH                                      1.055                                                                            CH.sub.2 CHCH.sub.2                                                                    CH.sub.2 CHCH.sub.2                                                                   H    H  OCH.sub.3                                                                          OCHF.sub.2                                                                         CH                                      1.056                                                                            CH.sub.2 CHCH.sub.2                                                                    CH.sub.2 CHCH.sub.2                                                                   H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH 136-138                              1.057                                                                            CH.sub.2 CHCH.sub.2                                                                    CH.sub.2 CHCH.sub.2                                                                   H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N                                       1.058                                                                            CH.sub.2 CHCH.sub.2                                                                    CH.sub.2 CHCH.sub.2                                                                   H    H  OC.sub.2 H.sub.5                                                                   CH.sub.3                                                                           N                                       1.059                                                                            CH.sub.2 CHCH.sub.2                                                                    CH.sub.2 CHCH.sub.2                                                                   H    H  OCH.sub.3                                                                          Cl   CH                                      1.060                                                                            HCCCH.sub.2                                                                            H       H    H  OCH.sub.3                                                                          Cl   CH                                      1.061                                                                            HC CCH.sub.2                                                                           H       H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH 155-157                              1.062                                                                            HCCCH.sub.2                                                                            H       H    H  OCHF.sub.2                                                                         OCHF.sub.2                                                                         CH                                      1.063                                                                            HCCCH.sub.2                                                                            H       H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N                                       1.064                                                                            HCCCH.sub.2                                                                            H       H    H  OC.sub.2 H.sub.5                                                                   CH.sub.3                                                                           N  132-134                              1.065                                                                            H        H       6-CH.sub.3                                                                         H  OCH.sub.3                                                                          CH.sub.3                                                                           N                                       1.066                                                                            H        H       H    H  OCH.sub.3                                                                          Cl   CH                                      1.067                                                                            H        H       H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.068                                                                            CH.sub.3 H       H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.069                                                                            CH.sub.3 H       H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N                                       1.070                                                                            CH.sub.3 CH.sub.3                                                                              H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N                                       1.071                                                                            CH.sub.3 CH.sub.3                                                                              H    H  OCH.sub.3                                                                          Cl   CH                                      1.072                                                                            C.sub.2 H.sub.5                                                                        H       H    H  OCH.sub.3                                                                          Cl   CH                                      1.073                                                                            C.sub.2 H.sub.5                                                                        H       H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N                                       1.074                                                                            CH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                              H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N                                       1.075                                                                            CH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                              H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.076                                                                            CH(CH.sub.3).sub.2                                                                     CH.sub.3                                                                              H    H  OCH.sub.3                                                                          Cl   CH                                      1.077                                                                            CH.sub.3 CH.sub.3                                                                              H    H  CH.sub.3                                                                           OCH.sub.3                                                                          CH 126-128                              1.078                                                                            (CH.sub.2).sub.5 H    H  CH.sub.3                                                                           OCH.sub.3                                                                          N  138-140                              1.079                                                                            (CH.sub.2).sub.5 H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH 126-130                              1.080                                                                            (CH.sub.2).sub.5 H    H  OCH.sub.3                                                                          CH.sub.3                                                                           CH                                      1.081                                                                            (CH.sub.2).sub.5 H    H  CH.sub.3                                                                           CH.sub.3                                                                           CH                                      1.082                                                                             ##STR20##       H    H  CH.sub.3                                                                           CH.sub.3                                                                           N  166-168                              1.083                                                                             ##STR21##       H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.084                                                                            (CH.sub.2).sub.2 O(CH.sub.2).sub.2                                                             H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N  148-150                              1.085                                                                            (CH.sub.2).sub.2 O(CH.sub.2).sub.2                                                             H    H  OCH.sub.3                                                                          CH.sub.3                                                                           CH                                      1.086                                                                            (CH.sub.2).sub.2 O(CH.sub.2).sub.2                                                             H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH 156-159                              1.087                                                                            CH.sub.2 CH(CH.sub.3).sub.2                                                            H       H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N  131-133                              1.088                                                                            CH.sub.2 CH(CH.sub.3).sub.2                                                            H       H    H  OCH.sub.3                                                                          CH.sub.3                                                                           CH                                      1.089                                                                            CH.sub.2 CH(CH.sub.3).sub.2                                                            H       H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH 110-114                              1.090                                                                            C.sub.6 H.sub.13 (n)                                                                   H       H    H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH 112-114                              1.091                                                                            C.sub.6 H.sub.13 (n)                                                                   H       H    H  OCH.sub.3                                                                          CH.sub.3                                                                           CH                                      1.092                                                                            C.sub.6 H.sub.13 (n)                                                                   H       H    H  OCH.sub.3                                                                          CH.sub.3                                                                           N  100-102                              1.093                                                                            CH.sub.2 CH(CH.sub.3).sub.2                                                            H       H    H  OCH.sub.3                                                                          Cl   CH 108-109                              1.094                                                                            CH(CH.sub.3).sub.2                                                                     H       H    H  CH.sub.3                                                                           OCHF.sub.2                                                                         CH 70-72                                1.095                                                                            CH(CH.sub.3).sub.2                                                                     H       H    H  CH.sub.3                                                                           CH.sub.3                                                                           CH 145-147                              1.096                                                                            CH.sub.3 CH.sub.3                                                                              H    H  CH.sub.3                                                                           CH.sub.3                                                                           CH 132- 135                             1.097                                                                            HCCCH.sub.2                                                                            H       H    H  CH.sub.3                                                                           OCH.sub.3                                                                          CH 157-159                              1.098                                                                            HCCCH.sub.2                                                                            H       H    H  CH.sub.3                                                                           CH.sub.3                                                                           CH 150-151                              1.099                                                                            CH.sub.3 CH.sub.3                                                                              6-CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.100                                                                            CH.sub.3 CH.sub.3                                                                              6-CH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                                                          CH                                      1.101                                                                            CH.sub.3 CH.sub.3                                                                              6-CH.sub.3                                                                         H  Cl   OCH.sub.3                                                                          CH                                      1.102                                                                            CH.sub.3 CH.sub.3                                                                              6-CH.sub.3                                                                         H  OCHF.sub.2                                                                         OCH.sub.3                                                                          CH                                      1.103                                                                            CH.sub.3 CH.sub.3                                                                              6-CH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                                                          N                                       1.104                                                                            CH.sub.3 H       6-CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.105                                                                            CH.sub.3 H       6-CH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                                                          CH                                      1.106                                                                            CH.sub.3 H       6-CH.sub.3                                                                         H  Cl   OCH.sub.3                                                                          CH                                      1.107                                                                            CH.sub.3 H       6-CH.sub.3                                                                         CH.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.108                                                                            C.sub.2 H.sub.5                                                                        CH.sub.3                                                                              6-CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.109                                                                            C.sub.2 H.sub.5                                                                        CH.sub.3                                                                              6-CH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                                                          CH                                      1.110                                                                            C.sub.2 H.sub.5                                                                        CH.sub.3                                                                              6-CH.sub.3                                                                         H  CH.sub.3                                                                           CH.sub.3                                                                           CH                                      1.111                                                                            C.sub.2 H.sub.5                                                                        H       6-CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.112                                                                            C.sub.2 H.sub.5                                                                        H       6-CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                          N                                       1.113                                                                            C.sub.2 H.sub.5                                                                        H       6-CH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                                                          CH                                      1.114                                                                            CH.sub.3 CH.sub.3                                                                              5-CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.115                                                                            CH.sub.3 CH.sub.3                                                                              5-CH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                                                          CH                                      1.116                                                                            CH.sub.3 H       5-CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.117                                                                            C.sub.2 H.sub.5                                                                        H       5-CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.118                                                                            C.sub.2 H.sub.5                                                                        CH.sub.3                                                                              5-CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.119                                                                            CH.sub.3 CH.sub.3                                                                              4-CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.120                                                                            CH.sub.3 H       4-CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.121                                                                            C.sub.2 H.sub.5                                                                        H       4-CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.122                                                                            C.sub.2 H.sub.5                                                                        CH.sub.3                                                                              4-CH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.123                                                                            CH.sub.3 CH.sub.3                                                                              6-OCH.sub.3                                                                        H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.124                                                                            CH.sub.3 CH.sub.3                                                                              6-OCH.sub.3                                                                        H  OCH.sub.3                                                                          CH.sub.3                                                                           CH                                      1.125                                                                            CH.sub.3 CH.sub.3                                                                              6-OCH.sub.3                                                                        H  Cl   OCH.sub.3                                                                          CH                                      1.126                                                                            CH.sub.3 CH.sub.3                                                                              6-OCH.sub.3                                                                        H  OCHF.sub.2                                                                         OCHF.sub.2                                                                         CH                                      1.127                                                                            CH.sub.3 CH.sub.3                                                                              6-OCH.sub.3                                                                        H  CH.sub.3                                                                           OCH.sub.3                                                                          N                                       1.128                                                                            CH.sub.3 H       6-OCH.sub.3                                                                        H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.129                                                                            CH.sub.3 H       6-OCH.sub.3                                                                        H  CH.sub.3                                                                           OCH.sub.3                                                                          CH                                      1.130                                                                            CH.sub.3 H       6-OCH.sub.3                                                                        H  Cl   OCH.sub.3                                                                          CH                                      1.131                                                                            CH.sub.3 H       6-OCH.sub.3                                                                        CH.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.132                                                                            C.sub.2 H.sub.5                                                                        CH.sub.3                                                                              6-OCH.sub.3                                                                        H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.133                                                                            C.sub.2 H.sub.5                                                                        CH.sub.3                                                                              6-OCH.sub.3                                                                        H  CH.sub.3                                                                           OCH.sub.3                                                                          CH                                      1.134                                                                            C.sub.2 H.sub.5                                                                        CH.sub.3                                                                              6-OCH.sub.3                                                                        H  CH.sub.3                                                                           CH.sub.3                                                                           CH                                      1.135                                                                            C.sub.2 H.sub.5                                                                        H       6-OCH.sub.3                                                                        H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.136                                                                            C.sub.2 H.sub.5                                                                        H       6-OCH.sub.3                                                                        H  OCH.sub.3                                                                          OCH.sub.3                                                                          N                                       1.137                                                                            C.sub.2 H.sub.5                                                                        H       6-OCH.sub.3                                                                        H  CH.sub.3                                                                           OCH.sub.3                                                                          CH                                      1.138                                                                            CH.sub.3 CH.sub.3                                                                              6-OCHF.sub.2                                                                       H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.139                                                                            CH.sub.3 H       6-OCHF.sub.2                                                                       H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.140                                                                            C.sub.2 H.sub.5                                                                        CH.sub.3                                                                              6-OCHF.sub.2                                                                       H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.141                                                                            CH.sub.3 CH.sub.3                                                                              5-Cl H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.142                                                                            CH.sub.3 CH.sub.3                                                                              5-Cl H  CH.sub.3                                                                           OCH.sub.3                                                                          CH                                      1.143                                                                            CH.sub.3 H       5-Cl H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.144                                                                            CH.sub.3 CH.sub.3                                                                              5-CF.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.145                                                                            CH.sub.3 H       4-CF.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      1.146                                                                            CH.sub.3 CH.sub.3                                                                              4-CF.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                      __________________________________________________________________________

                  TABLE 2                                                         ______________________________________                                         ##STR22##                    (II)                                                                                  M.p.                                    No.  R.sub.1      R.sub.2      R.sub.3                                                                              [°C.]                            ______________________________________                                        2.001                                                                              n-C.sub.4 H.sub.9                                                                          H            H      100-101                                 2.002                                                                              CH.sub.2 CHCH.sub.2                                                                        H            H      134-135                                 2.003                                                                              H            H            H      186-188                                 2.004                                                                              CH.sub.3     H            H      147-148                                 2.005                                                                              CH.sub.3     CH.sub.3     H      111-113                                 2.006                                                                              C.sub.2 H.sub.5                                                                            H            H      149-150                                 2.007                                                                              CH(CH.sub.3).sub.2                                                                         H            H      96-97                                   2.008                                                                              C.sub.2 H.sub.5                                                                            CH.sub.3     H      79-80                                   2.009                                                                              CH(CH.sub.3).sub.2                                                                         CH.sub.3     H      128-130                                 2.010                                                                         (n)-C.sub.4 H.sub.9                                                                CH.sub.3     H            Oil                                            2.011                                                                              CH.sub.2 CHCH.sub.2                                                                        CH.sub.2 CHCH.sub.2                                                                        H      75-76                                   2.012                                                                              HCCCH.sub.2  H            H      157-158                                 2.013                                                                              H            H            6-CH.sub.3                                     2.014                                                                              H            H            6-OCH.sub.3                                    2.015                                                                              CH.sub.3     H            6-CH.sub.3                                     2.016                                                                              CH.sub.3     CH.sub.3     6-CH.sub.3                                     2.017                                                                              CH(CH.sub.3).sub.2                                                                         H            6-CH.sub.3                                     2.018                                                                              CH(CH.sub.3).sub.2                                                                         CH.sub.3     6-CH.sub.3                                     2.019                                                                              CH.sub.3 OCH.sub.2 CH.sub.2                                                                H            H                                              2.020                                                                              CH.sub.3 OCH.sub.2 CH.sub.2                                                                CH.sub.3     H                                              2.021                                                                              (CH.sub.3).sub.2 NCH.sub.2 CH.sub.2                                                        H            H                                              2.022                                                                              (CH.sub.3).sub.2 NCH.sub.2 CH.sub.2                                                        CH.sub.3     H                                              2.023                                                                              (CH.sub.2).sub.5      H        183-184                                   2.024                                                                               ##STR23##            H        211-212                                   2.025                                                                              (CH.sub.2).sub.2 O(CH.sub.2).sub.2                                                                  H        193-194                                   2.026                                                                              H            CH.sub.2 CH(CH.sub.3).sub.2                                                                H      107-108                                 2.027                                                                              H            C.sub.6 H.sub.13 (n)                                                                       H      107-108                                 2.028                                                                              CH.sub.3     CH.sub.3     6-CH.sub.3                                     2.029                                                                              CH.sub.3     H            6-CH.sub.3                                     2.030                                                                              C.sub.2 H.sub.5                                                                            CH.sub.3     6-CH.sub.3                                     2.031                                                                              C.sub.2 H.sub.5                                                                            H            6-CH.sub.3                                     2.032                                                                              CH.sub.3     CH.sub.3     6-OCH.sub.3                                    2.033                                                                              CH.sub.3     H            6-OCH.sub. 3                                   2.034                                                                              C.sub.2 H.sub.5                                                                            CH.sub.3     6-OCH.sub.3                                    2.035                                                                              C.sub.2 H.sub.5                                                                            H            6-OCH.sub.3                                    2.036                                                                              CH.sub.3     CH.sub.3     5-CH.sub.3                                     2.037                                                                              CH.sub.3     H            5-CH.sub.3                                     2.038                                                                              C.sub.2 H.sub.5                                                                            CH.sub.3     5-CH.sub.3                                     2.039                                                                              C.sub.2 H.sub.5                                                                            H            5-CH.sub.3                                     2.040                                                                              CH.sub.3     CH.sub.3     4-CH.sub.3                                     2.041                                                                              CH.sub.3     H            4-CH.sub.3                                     2.042                                                                              C.sub.2 H.sub.5                                                                            CH.sub.3     4-CH.sub.3                                     2.043                                                                              C.sub.2 H.sub.5                                                                            H            4-CH.sub.3                                     2.044                                                                              CH.sub.3     CH.sub.3     6-OCHF.sub.2                                   2.045                                                                              CH.sub.3     H            6-OCHF.sub.2                                   2.046                                                                              C.sub.2 H.sub.5                                                                            CH.sub.3     6-OCHF.sub.2                                   2.047                                                                              CH.sub.3     CH.sub.3     5-Cl                                           2.048                                                                              CH.sub.3     H            5-Cl                                           2.049                                                                              CH.sub.3     CH.sub.3     5-CF.sub.3                                     2.050                                                                              CH.sub.3     H            4-CF.sub.3                                     2.051                                                                              CH.sub.3     CH.sub.3     4-CF.sub.3                                     ______________________________________                                    

BIOLOGICAL EXAMPLES EXAMPLE B 1 Herbicidal action before emergence ofthe plants

Plastic pots are filled with expanded vermiculite (density: 0.135 g/cm³,water adsorption capacity: 0.565 l/l). After the non-adsorptivevermiculite has been saturated with an aqueous emulsion of activesubstance in deionised water, containing the active substances at aconcentration of 70.8 ppm, seeds of the following plants are sown on thesurface: Nasturtium officinalis, Agrostis tenuis, Stellaria media andDigitaria sanguinalis. The test containers are subsequently kept in acontrolled-environment cabinet at a temperature of 20° C., anillumination of approx. 20 klux and a relative atmospheric humidity of70%. During a germination phase of 4 to 5 days, the pots are coveredwith transparent material to increase the local atmospheric humidity,and watered with deionised water. After day 5, 0.5% of a commerciallyavailable liquid fertiliser is added to the irrigation water. 12 daysafter sowing, the test is evaluated, and the action on the test plantsis assessed using the following scale:

1: plant not germinated or completely dead

2-3: powerful action

4-6: medium action

7-8: weak action

9: no action (like untreated control)

                  TABLE B1                                                        ______________________________________                                        Pre-emergence action:                                                         Concentration of the emulsion of active substance: 70.8 ppm                   Active substance                                                                          Test plant:                                                       No.         Nasturtium                                                                              Stellaria                                                                              Agrostis                                                                             Digitaria                               ______________________________________                                        1.001       1         3        1      3                                       1.008       2         2        2      2                                       1.012       1         2        1      2                                       1.013       1         1        1      2                                       1.014       2         2        2      2                                       1.017       1         2        1      2                                       1.018       2         3        2      2                                       1.019       2         2        1      2                                       1.023       1         2        1      3                                       1.027       1         1        1      2                                       1.043       1         1        1      2                                       ______________________________________                                    

EXAMPLE B 2 Post-emergence herbicidal action (contact herbicide)

A number of weeds, both monocotyledon and dicotyledon, are sprayed afteremergence (in the 4- to 6-leaf stage) with an aqueous dispersion ofactive substance at a dosage rate of 8-500 g of active substance perhectare, and the plants are kept at 24°-26° C. and 45-60% relativeatmospheric humidity.

After 3 weeks, the herbicidal action is assessed using a nine-step key(1=complete damage, 9=no action) in comparison with an untreated controlgroup. Scores from 1 to 4 (in particular 1 to 3) suggest a good to verygood herbicidal action. Scores from 6 to 9 (in particular from 7 to 9)suggest a good tolerance (in particular in the case of crop plants).

In this test, the compounds of the formula I show a powerful herbicidalaction.

EXAMPLE B 3 Herbicidal action for paddy rice

The aquatic weeds Echinochloa crus galli and Monocharia vag. are sown inplastic beakers (surface area 60 cm², volume 500 ml). After sowing, thebeakers are filled with water up to the soil surface. 3 days aftersowing, the water level is increased to slightly above soil level (3-5mm). The application is carried out 3 days after sowing, by spraying thecontainers with the test substances. The dosage rate used corresponds toan amount of active substance of 500 g of A.S. per hectare. The beakerswith the plants are then placed in the greenhouse under optimum growthconditions for the rice weeds, i.e. at 25°-30° C. and high atmospherichumidity.

The tests are evaluated 3 weeks after application. In these tests, thecompounds of the formula I damage the weeds.

    ______________________________________                                        Formulation examples of active substances of the formula I                    (% = percent by weight)                                                       1. Wettable powder a)       b)      c)                                        ______________________________________                                        Active substance from Table 1                                                                    20%      50%       0.5%                                    Na ligninsulfonate 5%       5%      5%                                        Na lauryl sulfate  3%       --      --                                        Na diisobutylnaphthalenesulfonate                                                                --       6%      6%                                        Octylphenol polyethylene glycol                                                                  --       2%      2%                                        ether (7-8 mol of EO)                                                         Highly-disperse silica                                                                           5%       27%     27%                                       Kaolin             67%      --      --                                        Sodium chloride    --       --       59.5%                                    ______________________________________                                    

The active substance is thoroughly mixed with the additives andthoroughly ground in a suitable mill. This gives wettable powders whichcan be diluted with water to give suspensions of any desiredconcentration.

    ______________________________________                                        2. Emulsion concentrates                                                                             a)      b)                                             ______________________________________                                        Active substance from Table 1                                                                        10%     1%                                             Ca dodecylbenzenesulfonate                                                                           3%      3%                                             Octylphenol polyethylene glycol ether                                                                3%      3%                                             (4-5 mol of EO)                                                               Castor oil polyethylene glycol ether                                                                 4%      4%                                             (36 mol of EO)                                                                Cyclohexanone          30%     10%                                            Xylene mixture         50%     79%                                            ______________________________________                                    

Emulsions of any desired concentration can be prepared from suchconcentrates by diluting them with water.

    ______________________________________                                        3. Dusts             a)      b)                                               ______________________________________                                        Active substance from Table 1                                                                       0.1%    1%                                              Talc                 99.9%    1%                                              Kaolin               --      99%                                              ______________________________________                                    

Ready-to-use dusts are obtained by intimately mixing the carrier withthe active substance.

    ______________________________________                                        4. Extruder granules a)      b)                                               ______________________________________                                        Active substance from Table 1                                                                      10%     1%                                               Na ligninsulfonate    2%     2%                                               Carboxymethylcellulose                                                                              1%     1%                                               Kaolin               87%     96%                                              ______________________________________                                    

The active substance is mixed with the additives, and the mixture isground and moistened with water. This mixture is extruded andsubsequently dried in a stream of air.

    ______________________________________                                        5. Coated granules                                                            ______________________________________                                        Active substance from Table 1                                                                      3%                                                       Polyethylene glycol (MW 200)                                                                       3%                                                       Kaolin               94%                                                      ______________________________________                                    

The kaolin is moistened with polyethylene glycol and the finely-groundactive substance is applied uniformly thereto in a mixer. Dust-freecoated granules are obtained in this manner.

    ______________________________________                                        6. Suspension concentrate                                                                            a)      b)                                             ______________________________________                                        Active substance from Table 1                                                                        5%      40%                                            Ethylene glycol        10%     10%                                            Nonylphenol polyethylene                                                                             1%       6%                                            glycol ether (15 mol of EO)                                                   Na ligninsulfonate     5%      10%                                            Carboxymethylcellulose 1%       1%                                            37% aqueous formaldehyde solution                                                                      0.2%    0.2%                                         Silicone oil in the form of a 75% aqueous                                                              0.8%    0.8%                                         emulsion                                                                      Water                  77%     32%                                            ______________________________________                                    

The finely-ground active substance is mixed intimately with theadditives. This gives a suspension concentrate, from which suspensionsof any desired concentration can be prepared by diluting it with water.

    ______________________________________                                        7. Salt solution                                                              ______________________________________                                        Active substance from Table 1                                                                         5%                                                    Isopropylamine          1%                                                    Octylphenol polyethylene glycol ether                                                                 3%                                                    (78 mol of EO)                                                                Water                   91%                                                   ______________________________________                                    

The compounds of the formula I are employed as such or preferably ascompositions together with the auxiliaries customary in formulationtechnology, and they are therefore processed in a known manner to give,for example, emulsion concentrates, directly sprayable or dilutablesolutions, dilute emulsions, sprayable powders, soluble powders, dusts,granules, and also encapsulations, for example in polymeric substances.The application methods, such as spraying, atomising, dusting,scattering or pouring, as well as the type of compositions are selectedto suit the intended aims and the prevailing circumstances.

What is claimed is:
 1. A compound of the formula II ##STR24## in whichR₁ and R₂ independently of one another are hydrogen, C₁ -C₈ alkyl or C₃-C₈ cycloalkyl; C₂ -C₈ alkyl or C₃ -C₈ cycloalkyl, each of which issubstituted by halogen; C₁ -C₈ alkyl or C₃ -C₈ cycloalkyl, each of whichis substituted by --NR₅ R₆, C₁ -C₄ alkoxy or C₁ -C₄ alkyl--S(O)_(n) --;C₁ -C₄ alkyl or C₃ -C₆ cycloalkyl, each of which is substituted by C₂-C₄ alkenyl, C₅ -C₆ cycloalkenyl, C₂ -C₆ alkynyl or C₄ -C₈ alkadienyl,wherein the C₂ -C₄ alkenyl, C₅ -C₆ cycloalkenyl or C₄ -C₈ alkadienylradicals are optionally substituted by halogen; or R₁ and R₂ togetherare a 4-5-membered C₄ -C₁₀ alkylene chain which can be interrupted byoxygen, sulfur or N--R₇ ; R₃ is hydrogen, halogen, C₁ -C₄ alkyl, C₁ -C₄alkoxy or C₁ -C₄ alkylthio; or C₁ -C₄ alkyl, C₁ -C₄ alkoxy or C₁ -C₄alkylthio which is substituted by halogen; R₅, R₆ and R₇ independentlyof one another are hydrogen or C₁ -C₄ alkyl, and n is 0, 1 or 2; withthe provisos that R₁, R₂ and R₃ are not simultaneously hydrogen and thatR₁ and R₂ are not simultaneously hydrogen when R₃ is C₁ -C₄ alkyl.
 2. Acompound of the formula II according to claim 1, in which R₁ and R₂independently of one another are hydrogen, C₁ -C₈ alkyl or C₃ -C₈cycloalkyl; C₂ -C₈ alkyl or C₃ -C₈ cycloalkyl which are substituted byhalogen; C₁ -C₈ alkyl or C₃ -C₈ cycloalkyl which are substituted by--NR₅ R₆, C₁ -C₄ alkoxy or C₁ -C₄ alkyl--S(O)_(n) --; C₁ -C₄ alkyl or C₃-C₆ cycloalkyl which are substituted by C₂ -C₄ alkenyl, C₅ -C₆cycloalkenyl, C₂ -C₆ alkynyl or C₄ -C₈ alkadienyl, wherein the C₂ -C₄alkenyl, C₅ -C₆ cycloalkenyl or C₄ -C₈ alkadienyl radicals areoptionally substituted by halogen; or R₁ and R₂ together are a4-5-membered C₄ -C₅ alkylene chain which can be interrupted by oxygen,sulfur or N--R₇.
 3. A compound of the formula II according to claim 1,in which R₁ and R₂ independently of one another are hydrogen, C₁ -C₈alkyl or C₃ -C₈ cycloalkyl; C₂ -C₈ alkyl or C₃ -C₈ cycloalkyl which aresubstituted by halogen; C₁ -C₈ alkyl or C₃ -C₈ cycloalkyl which aresubstituted by --NR₅ R₆, C₁ -C₄ alkoxy or C₁ -C₄ alkyl--S(O)_(n) --; C₁-C₄ alkyl or C₃ -C₆ cycloalkyl which are substituted by C₂ -C₄ alkenyl,C₅ -C₆ cycloalkenyl, C₂ -C₆ alkynyl or C₄ -C₈ alkadienyl, wherein the C₂-C₄ alkenyl, C₅ -C₆ cycloalkenyl or C₄ -C₈ alkadienyl radicals areoptionally substituted by halogen.
 4. A compound of the formula IIaccording to claim 1, in which R₁ and R₂ independently of one anotherare hydrogen, C₁ -C₆ alkyl or C₃ -C₆ cycloalkyl; C₂ -C₆ alkyl or C₃ -C₆cycloalkyl which are monosubstituted to trisubstituted by halogen; C₁-C₆ alkyl or C₃ -C₆ cycloalkyl which are substituted by --NR₅ R₆, C₁ -C₄alkoxy or C₁ -C₄ alkyl--S(O)_(n) --; C₁ -C₄ alkyl or C₃ -C₆ cycloalkylwhich are substituted by C₂ -C₄ alkenyl, C₅ -C₆ cycloalkenyl, C₂ -C₄alkynyl or C₄ -C₈ alkadienyl, wherein the C₂ -C₄ alkenyl, C₅ -C₆cycloalkenyl or C₄ -C₈ alkadienyl radicals are optionallymonosubstituted to trisubstituted by halogen; and R₃ is hydrogen,halogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy or C₁ -C₄ alkylthio; or C₁ -C₄alkyl, C₁ -C₄ alkoxy or C₁ -C₄ alkylthio which are monosubstituted totrisubstituted by halogen.
 5. A compound of the formula II according toclaim 1, in which R₃ is in the 6-position of the pyridine ring.
 6. Acompound of the formula II according to claim 1, in which R₃ ishydrogen.
 7. A compound of the formula II according to claim 1, in whichR₂ and R₃ are hydrogen and R₁ is C₁ -C₆ alkyl or C₃ -C₆ cycloalkyl; C₂-C₆ alkyl or C₃ -C₆ cycloalkyl which are monosubstituted totrisubstituted by halogen; C₁ -C₆ alkyl or C₃ -C₆ cycloalkyl which aresubstituted by --NR₅ R₆, C₁ -C₄ alkoxy or C₁ -C₄ alkyl--S(O)_(n) --; C₁-C₄ alkyl or C₃ -C₆ cycloalkyl which are substituted by C₂ -C₄ alkenyl,C₅ -C₆ cycloalkenyl, C₂ -C₄ alkynyl or C₄ -C₈ alkadienyl, wherein the C₂-C₄ alkenyl, C₅ -C₆ cycloalkenyl or C₄ -C₈ alkadienyl radicals areoptionally monosubstituted to trisubstituted by halogen.
 8. A compoundof the formula II according to claim 24, in which R₁ is C₁ -C₆ alkyl,allyl or propargyl, and R₂ is hydrogen, methyl or allyl. 9.3-n-Butylaminopyridin-2-ylsulfonamide according to claim 7.